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Call for ContributionsHETEROCYCLES Special Issue Vol. 99 in honor of Professor Tohru Fukuyama on 70th Birthday

Submission deadline: September 10, 2018
On the occasion of Professor Tohru Fukuyama's 70th birthday, HETEROCYCLES editorial office is planning to publish special anniversary issue on April 1, 2019 as Vol. 99. Authors are invited to submit their work to this topical issue.
Authors wishing to submit their manuscript should contact editorial office via e-mail by the end of May, 2018. Manuscript should reach the editorial office no later than September 10, 2018.
Contact: submit@heterocycles.com

March 5, 2018

Heterocycles Award
HETEROCYCLES is pleased to announce Heterocycles Award.
In recognition of an outstanding oral presentation at the 47th Congress of Heterocyclic ChemistrySee more

December 13, 2017

Call for ContributionsHETEROCYCLES Special Issue Vol. 97 in honor of Professor Kiyoshi Tomioka on 70th Birthday

Submission deadline: February 15, 2018
On the occasion of Professor Kiyoshi Tomioka's 70th birthday, HETEROCYCLES editorial office is planning to publish special anniversary issue on September 1, 2018 as Vol. 97. Authors are invited to submit their work to this topical issue.
Authors wishing to submit their manuscript should contact editorial office via e-mail by the end of November, 2017. Manuscript should reach the editorial office no later than February 15, 2018.
Contact: submit@heterocycles.com

■ Total Syntheses of Liphagal: A Potent and Selective Phosphoinositide 3-Kinase α (PI3Kα) Inhibitor from the Marine Sponge Aka coralliphaga

Abstract

Liphagal, isolated from the marine sponge Aka coralliphaga, exhibits a potent and selective inhibitory activity against phosphoinositide 3-kinase α (PI3Kα). This marine natural product has attracted significant attention because of its potential as a promising candidate or new lead for the development of novel molecular targeted anticancer agents. In this review, the reported total syntheses of liphagal are presented with a particular focus on the methodologies and strategies employed.

Abstract

A mild and efficient method for the synthesis of chromenonaphthyridine derivatives via domino reaction of aminopyridine and different O-propargylated salicylaldehydes using CuI/InCl3 as an efficient catalyst, refluxed in acetonitrile is reported. Mild reaction condition, operational simplicity, good to excellent yield and easy isolation of product is the silent feature of this reaction.

■ A Facile Synthesis of Novel Heterocyclic Compounds with Anticipated Antibacterial Activities Based on Coumarin Moiety

Abstract

A novel series of coumarin derivatives has been disclosed by allowing 2-aminonicotinonitrile derivative 1 to undergo alkylation, diazotization, and condensation reactions. Moreover, different reagents, such as thiourea, phenyl isothiocyanate, carbon disulfide, ethylenediamine, and hydroxylamine hydrochloride, have been exploited to synthesize more coumarin derivatives, aiming to increase the synthetic potential of coumarin and study the antibacterial activities of the newly synthesized compounds.

■ A Convenient Synthesis of Indole and 1,4-Dihydropyridine Hybrid Macromolecules by Dimerization of [2-(1H-Indol-3-yl)ethyl]pyridinium Salts

Abstract

The design and synthesis of a novel type of macrocyclic compounds containing indole and 1,4-dihydropyridine heterocyclic subunits is presented. The key reaction involved in the synthesis was a base-mediated dimerization of [2-(1H-indol-3-yl)ethyl]pyridinium salts. The structure of the macrocycles was unambiguously confirmed by NMR and HRMS spectroscopic and X-ray singlecrystal diffraction.

Abstract

We design and synthesize a series of novel pyrazole amides based on the commercialized fungicides and our previous work. The antifungal activity was tested in vitro by mycelial growth inhibition assay. The results show that all the compounds are of antifungal activities against the tested fungi at different levels. Among them, N-(2-(7-bromo-5-chloro-1H-indazol-1-yl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Vk) exhibited higher antifungal activity than boscalid against two fungi. Molecular docking study revealed that the carbonyl oxygen atom of Vk forms two hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.

Abstract

Bis(thiazol-5-yl)phenyl- and bis(thiazol-5-yl)methanes were synthesized by the reaction of 2,4-disubstituted thiazoles with aromatic aldehydes or formaldehyde. In addition, modification of the carboxyl group of the molecule was carried out. The reactions afforded compounds bearing various heterocyclic fragments. All the synthesized compounds were tested for their effect onEscherichia coli, Staphylococcus aureus and Mycobacterium luteum bacteria and Aspergillus niger and Candida tenuis fungi strains. Some of them exhibited antibacterial activity against test-culture Mycobacterium luteum.

Abstract

Novel C4-linked triazol C0-, C1- and C2-ribonucleoside phosphoramidites for RNA catalysis probing were synthesized from β-ribofuranosyl-Cn-acetylenes (n = 0–2), which were efficiently prepared by fragmentation of tetrazoles derived from cyanophosphates. N-Pivaloyloxymethyl moiety was selected for the protection of triazole-N, whose properties under acidic and basic conditions were investigated.

Abstract

Thromboxane A2, a potent platelet aggregation factor, contains a labile 2,6-dioxabicyclo[3.1.1]heptane as the core moiety. Dibromo compounds with a similar core structure were synthesized by the cyclization of tribromides derived from D-glucal.

Abstract

Three new flavones (1–3), together with six known flavones (4–9), were isolated from the fruits of Vernicia fordii collected from Hunan province of China. Their structures were characterized by means of extensive spectroscopic analyses. Compounds 1–3and 9were evaluated for their anti-tobacco mosaic virus (anti-TMV) activity. The results showed that compound 9 exhibited high anti-TMV activity with inhibition rate of 32.6%. This inhibition rate is close to that of positive control (33.8%). Compounds 1–3 also showed potential anti-TMV activities with inhibition rates of 26.8%, 29.2%, and 25.7%, respectively.

Abstract

We report the preparation of newly designed trivalent C3-symmetrical cyclic phenylboronic acid derivatives constructed on a symmetrical benzene or a cyclohexane ring. The synthesis of these C3-symmetrical molecules 4 was accomplished by an amide bond formation reaction using amino-substituted phenylboronic acid pinacol esters 2 and C3-symmetrical benzene-1,3,5-tricarboxylic acid trichloride 3a or cyclohexane-1,3,5-tricarboxylic acid trichloride 3b in the presence of Et3N. We confirmed that this procedure is conventionally applicable to the preparation of targeted C3-symmetrical cyclic boronic acid derivatives 4 in good to excellent yields. We also report the results of biological evaluation of the prepared compounds.

Abstract

A diastereospecific intramolecular cyclopropanation of (3R,8R,8aS)-8-bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-one 1 and (3R,8S,8aS)-8-bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-one 2 to generate the corresponding enantiopure 3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-ones 3 and 4 in high yield is described.